Straightforward synthesis of bioconjugatable azo dyes. Part 2: Black Hole Quencher-2 (BHQ-2) and BlackBerry Quencher 650 (BBQ-650) scaffolds |
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| Affiliation: | 1. Normandie Univ., COBRA, UMR 6014 & FR 3038, UNIV Rouen; INSA Rouen; CNRS, IRCOF, 1 Rue Tesnières, 76821 Mont-Saint-Aignan Cedex, France;2. ICMUB, UMR CNRS 6302, Université de Bourgogne, 9, Avenue Alain Savary, 21078 Dijon, France;3. Institut Universitaire de France, 103 Boulevard Saint-Michel, 75005 Paris, France;1. Department of Chemistry, South Ural State University, Russia;2. Department of Quantum Chemistry, D.I. Mendeleev University of Chemical Technology, Russia;1. Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan;2. Department of Chemistry, College of Sciences and Humanities, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia;3. Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland;4. Department of Physics, University of Sargodha, Sargodha, Pakistan;5. Department of Chemistry, Faculty of Science, University of Malaya, Lembah Pantai, 50603 Kuala Lumpur, Malaysia;6. Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia;7. Department of Chemistry, Government Dyal Singh College, Lahore, Pakistan |
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| Abstract: | A further extension of the efficient synthetic methodology described in Part 1, to the aromatic bis-diazo scaffold of Black Hole Quencher-2 dye is presented. Bioconjugatable derivatives bearing either azido, terminal alkyne, or maleimide reactive group were easily obtained as well as the free-phenol form of BlackBerry® Quencher 650 (BBQ-650®) initially developed by Berry & Associates, Inc. Company. The efficient conjugation ability of azido- and maleimide-quenchers was demonstrated through the facile preparation of the first water-soluble and formylated BHQ-2 dyes and a FRET-based probe suitable for the in vitro/in cellulo detection of a cancer-associated protease namely urokinase-type plasminogen activator. |
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| Keywords: | Activatable probes Azo dyes Bioconjugation Dark quenchers FRET |
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